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Deadly Valentines: The Story of Capone's Henchman

Deadly Valentines: The Story of Capone's Henchman "Machine Gun" Jack McGurn and Louise Rolfe, His Blonde Alibi

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by Jeffrey Gusfield

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Almost before the gunsmoke from the St. Valentine’s Day Massacre cleared, Chicago police had a suspect: Jack McGurn. They just couldn’t find him. McGurn, whose real name was Vincent Gebardi, was Al Capone’s chief assassin, a baby-faced Sicilian immigrant and professional killer of professional killers. But two weeks after the murders, police


Almost before the gunsmoke from the St. Valentine’s Day Massacre cleared, Chicago police had a suspect: Jack McGurn. They just couldn’t find him. McGurn, whose real name was Vincent Gebardi, was Al Capone’s chief assassin, a baby-faced Sicilian immigrant and professional killer of professional killers. But two weeks after the murders, police found McGurn and his paramour, Louise May Rolfe, holed up downtown at the Stevens Hotel. Both claimed they were in bed on the morning of the famous shootings, a titillating alibi that grabbed the public’s attention and never let go.

Deadly Valentines tells one of the most outrageous stories of the 1920s, a twin biography of a couple who defined the extremes and excesses of the Prohibition era in America. McGurn was a prizefighter, professional-level golfer, and the ultimate urban predator and hit man who put the iron in Al Capone’s muscle. Rolfe, a beautiful blonde dancer and libertine, was the epitome of fashion, rebellion, and wild abandon in the new jazz subculture. They were the prototypes for decades of gangster literature and cinema, representing a time that has never lost its allure.

Editorial Reviews

Publishers Weekly
Part history of the Capone era and part biography of one of Big Al’s top enforcers and his quintessential gangster’s moll, Gusfield’s book gives a thoroughly researched and colorful account of a bullet-ridden Jazz Age Chicago. Vincenzo Gibaldi immigrated from Sicily to the U.S. with his family as a four-year-old in 1906. Young Vincent was drawn to boxing and, taking the alias “Jack McGurn,” had moderate success in Chicago as an amateur welterweight. But McGurn’s other profession, with Al Capone’s “Outfit,” proved more lucrative: with his baby face and easygoing manner, McGurn was treated like an honorary Capone brother, known for precise and well-planned hits. He emerged into the spotlight when seven members of George “Bugs” Moran’s rival gang were brutally murdered in the St. Valentine’s Day Massacre. While no definitive proof exists that McGurn was one of the gunmen—Louise Rolfe, his hedonistic young lover embodying everything seductive about the Jazz Age, provided his alibi—Gusfield makes a strong case that he planned the attack. Despite the narrative being written annoyingly in the present tense, Gusfield portrays both McGurn and Rolfe as alluringly flawed and deadly in their own ways. 50 b&w photos. (Apr.)
From the Publisher

"[Gusfield] vividly tells the twisted, yet somehow moving love story of an iconic American gangster and his sexy, nutty gun moll. Told with a driving, you-are-there narrative, it's a rigorous, sometimes astonishing, and consistently entertaining performance."  —Douglas Perry, author of The Girls of Murder City: Fame, Lust, and the Beautiful Killers Who Inspired Chicago

 "Authoritative, fast-moving, and affecting,  Deadly Valentines tells a compelling true-life gangland saga that is loaded with action and, not least, the ache of romance. "  —Howard Blum, author of  American Lightning: Terror, Mystery, the Birth of Hollywood, and the Crime of the Century

"Skilled researcher and empathetic writer Gusfield steers us into the private world of Al Capone and the pugilist-turned-killer, Jack McGurn – their clannish roots and gangland alliances – and explores the Machiavellian power that Capone directs toward McGurn and his failed dream of ringside glory.  If the underworld ever produced an American tragedy, this is it."  —Ellen Poulsen, author of Don't Call Us Molls: Women of the John Dillinger Gang and The Case Against Lucky Luciano:  New York's Most Sensational Vice Trial

"Jeffrey Gusfield's Deadly Valentines is an encyclopedic love letter to the Roaring Twenties as embodied in its title characters, Jack McGurn and Louise Rolfe, each of whom succumbed to the seductive flash and drunken abandon of each other and the dark side of the American Dream. "  Paula Uruburu, author of American Eve: Evelyn Nesbit, Stanford White: The Birth of the "It" Girl and the Crime of the Century

"[Deadly Valentines is] a masterful attempt to find the facts about [McGurn], his second wife and alibi Louise Rolfe, and the events related to them. Gusfield is an engaging storyteller."  —John Binder, author of The Chicago Outfit

 "Deadly Valentines is not just a story of gangsters and guns, but of a love story that still captivates to this very day."  —Dan Waugh, author of Egan's Rats and Gangs of St. Louis: Men of Respect

"A thoroughly researched and colorful account." —Publishers Weekly

"[Deadly Valentines] is an engrossing look inside Al Capone's murderous ranks [and] a lively, detailed history of gangland Chicago." —Kirkus Reviews

Kirkus Reviews
Gusfield presents the short, brutal life of "Machine Gun" Jack McGurn (1902 –1936), born Vincent Gebardi, a gifted athlete who became notorious as Al Capone's deadliest lieutenant and putative organizer of the Saint Valentine's Day Massacre of 1929. In a parallel narrative, the author charts the dissolute history of Louise Rolfe, an archetypical jazz-baby flapper who, when liquored up behind the wheel, would prove nearly as fatal as her eventual paramour McGurn. Gusfield structures the book as the tale of the young lover's ill-starred romance, but the story is heavily weighted toward McGurn, whose natural toughness, intelligence and physical grace quickly elevated him in the ranks of the Capone organization, where he earned a reputation as a meticulous planner and devastatingly effective assassin. Gusfield provides a lively, detailed history of gangland Chicago in the 1920s, deftly parsing the intricate chains of betrayal and murder that drove the city's bootlegging trade and limning the era's swinging style and heat. The author perhaps overly idealizes McGurn, endlessly praising his boyish good looks, athletic gifts, taciturn implacability and ruthless efficiency--a climactic passage in which McGurn's dream of playing professional golf decisively collapses is rendered with the gravitas of Greek tragedy. Rolfe, portrayed here as essentially a spoiled, drunken nitwit, never resonates as a compelling character in her own right, making Gusfield's emphasis on their short-lived and unremarkable romance puzzling and giving his otherwise cleanly propulsive account a somewhat lopsided shape. McGurn would never have stood for such sloppiness. Still, an engrossing look inside Al Capone's murderous ranks and a chilling examination of a natural born killer.

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Chicago Review Press, Incorporated
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Read an Excerpt

Deadly Valentines

The Story of Capone's Henchman "Machine Gun" Jack McGurn and Louise Rolfe, His Blonde Alibi

By Jeffrey Gusfield

Chicago Review Press Incorporated

Copyright © 2012 Jeffrey Gusfield
All rights reserved.
ISBN: 978-1-61374-095-8


I Came to America to Give a Better Future to My Children


Giuseppa Verderame Gibaldi has brought the children to the main deck for their arrival in America; they huddle at the port railing of the steamship Gregory Morch. They are from warm Sicily and have never known such cold. Giuseppa has them wrapped in every piece of clothing they have, including blankets. They watch gulls and winter birds wheeling over the skies near the Sandy Hook lighthouse. Twenty minutes later, after passing through the narrows between Brooklyn and Staten Island, the Statue of Liberty appears, floating like the Madonna over the whitecapped harbor.

Baby Salvatore is in Giuseppa's arms, and she is holding four-year-old Vincenzo's little hand in a tight grip; he is an incredibly active toddler. Clinging to them is Giuseppa's eight-year-old brother, Francesco. They can hardly hear over the howling wind, the deep thrumming of the steam engines, and the echoes of the harbor horns. The chilling, salty wind whips through their ebony hair, which the Anglo ticket agents in Palermo describe as "maroon." They stare in wonderment at the signura virdi with her torch. They left Palermo on Thursday, November 7. Today — the day of their arrival at the port of New York — is Saturday, November 24. The four of them spent their eighteen-day journey in second cabin, a single stateroom with washing facilities, which was provided by Tommaso's money from America. It is almost a luxury accommodation compared to the steerage level that most Italian immigrants endure. Giuseppa has been watchdog, nurse, and mother to three little boys in an impossibly tiny space for over two weeks. She is strong, but still, the daunting task has worn her out. At times, she has certainly wondered if this is all worth the effort. The thought of dry land must be intoxicating.

Giuseppa will soon Americanize her name to Josephine. She has recorded her age on the passenger manifest as twenty-four, but in reality she is only nineteen. She claims to be older because she is towing three children alone. She has been warned that most Americans do not favor fifteen-year-olds having babies.

The father of her two boys, Tommaso Gibaldi, awaits the arrival of his family at 14 Union Street in Brooklyn, an apartment building that sits right on the apron of the docks. It is inhabited largely by immigrant men waiting for their families to arrive. Having preceded them to America, landing on April 19, 1903, Tommaso is now nineteen, born the same year as Giuseppa. He has slaved for twenty-two cents an hour for two and a half years as a longshoreman so he can bring his family over to America. He and his young wife want to escape the poverty and hopelessness of Sicily, where aspirations seem to wither, where Old World ways, cultures of vengeance, and murder remain the norm. They want to prosper without paying feudal extortion to Mafia or Black Hand criminals, who watch for signs of success like the familiar tarantulas that hide in wait to prey on fat insects. The Gibaldis desire a small place in America, where their hard work will move them forward in life, where their children will have choices, rewards, and freedom from tyranny.

Giuseppa sees Governor's Island as it appears on the right; ahead is Ellis Island. As the ship steers to port and enters the harbor, she turns toward the stern and surveys in wonderment the broken New York skyline. Everywhere she looks, the panorama is overwhelming. Her emotions wander from joy to awe to fear. America is already beyond anything she has imagined. She hugs Salvatore to her breast and squeezes Vincenzo's hand. She must feel tiny and insignificant, surrounded by the vast mountain range of concrete, smokestacks, and steel, with the unknown territories ahead.

Marked by cacophony and long waiting lines, the degrading and dehumanizing process of the immigrant arrival at Ellis Island awaits them. They are all questioned, examined, poked, and prodded, while Giuseppa struggles with the children. Her English is minimal. She tries her best to communicate with the officious American agents, who seem to have limited sympathy for the multitudes. There are only a handful of translators for the hundreds of Italians and none for the Sicilians. She juggles Salvatore, restrains Vincenzo, and keeps an eye on Francesco while the uniformed immigration Anglos hammer away at her.

She must think that perhaps she is losing her mind, especially as she physically fights to contain Vincenzo, whose energies seem endless. She yearns for Tommaso to help her as she brushes the tears from her cheeks, but he is waiting outside Ellis Island, having traveled there from Brooklyn, taking his first day off in many weeks to meet his family. He is terrified that he will lose his job on the docks, for there are hundreds of other newcomers ready to step in to replace him.

Many hours later, after the surreal torment blessedly ends, Giuseppa and all three boys prove themselves healthy and are released into their new world. Many others who have traveled with them remain quarantined on the island. Immigration doctors worry constantly about influenza, tuberculosis, and other diseases transmitted onto the mainland. At the end of a long promenade, Giuseppa spots Tommaso, a small man who now appears to be broader in his upper body from the hard labor. Giuseppa points him out to Vincenzo, and he runs to his father. Baby Salvatore was born after his father left for America; it is the first time Tommaso sees him. Nearly swooning with relief, Giuseppa weeps uncontrollably as she finally embraces her husband, as they become a new American family.

Before little Vincenzo Gibaldi lands in New York, his arma gemella, his soul mate, Louise May Rolfe, is born in Indianapolis on the seventh of May. Causing her eighteen-year-old mother, Mabel, to scream in agony, Louise is already making her pay. She is pink and bloody, with white hair and blue eyes that will remain blue. She is bathed and put into her mother's arms. Nobody could look at this beautiful baby and imagine how much trouble she will be, certainly not her momentarily happy parents.

Mabel Clark, a hopeful teenager whose mother was from Kansas and whose father was from Iowa, had married Bernard Frank Rolfe when she was sixteen. For the Clarks, an American version of the Victorian farm family, it was as if the sky had fallen and hell had erupted up through the corn, for Mabel married Bernard thinking she was pregnant. It turned out she was wrong: all those strange physical symptoms she was experiencing were from her first sexual encounter. The simple fear of her sins made her nearly hysterical. Her body reacted accordingly to the stress, fooling her, causing her to assume the worst.

Bernard Frank Rolfe, who was born in 1877 in Missouri, the Show Me state, asked pretty young Mabel to show him, and she did. He was handsome, and she was mesmerized. He was twenty-seven, and she, like many farm daughters, wanted desperately to get out of Iowa for a big city, full of life and culture. He had not yet learned that everybody is beautiful when they are young. They married under duress in a country church full of grim Midwestern faces.

Realizing full well that Mabel's people wanted to impale Bernard on a pitchfork, they ran from that stoic prairie wrath to Indianapolis, where Bernard had family. Bernard wanted to be in advertising; his vision of the new century was one of a retail and marketing heaven. He was a communicative talker and a first-rate salesman. Who else could get a sixteen-year old farmer's daughter to give up her virginity in her own father's barn?

After nine months in Indiana, she gives birth to Louise and presents her with the middle name of May, after herself and the joyful month. In the interim, Mabel has learned that Indianapolis isn't that much different from Des Moines; it's just another medium-size, provincial Midwestern town. She has yet to discover a true big city.

Six years later, Bernard, hungry to be in the advertising business that he finds so alluring, takes his young wife and daughter to Chicago. He becomes completely immersed in the world of selling and advertising anything and everything to the vast sea of eager new consumers in America's second largest city. While pregnant, Mabel gained sixty pounds, at least forty of which will remain with her. By the time they are ensconced on the North Side of Chicago, any affection Mabel and Bernard have for each other is evaporating like the morning mist on the Chicago River.


Sicily in Brooklyn


The Americanization of the Gibaldi family has begun. It is a difficult challenge for any greenhorn immigrant, although the very young seem to have an easier time of it. Vincenzo — which means the same thing as "James," more or less — refuses to be called anything other than Vincent. Salvatore becomes Sam, and Giuseppa is now Josephine.

Brooklyn days are far more challenging than she has ever anticipated. At night, however, cloistered in their tiny apartment at 9 Union Street, she tries to direct Vincent's dreams. Each evening she puts baby Sam to bed and then rocks Vincent to sleep in her arms, whispering of her Sicily.

Josephine has found the American immigrant experience daunting, even frightening at times. The culture shock is immense. She takes sweet comfort in verbally reconstructing Sicily for her children. She transfers to Vincent her world and her perceptions so that many of his first childhood memories are his mother's very best recollections. She wants him to remember the land of his birth, for she sees how America takes over the spirit. She senses that, with time, they will all completely forget their homeland.

Josephine and Tommaso had grown up in the little village of Licata, near Agrigento, the largest city on the southwestern coast of Sicily. Like most young people in their world, they had children at an age so tender that they hardly knew each other.

Tommaso Gibaldi came from a line of market haulers who brought fresh vegetables and fruits up and down the coast. Little Vincent has almost no memory of Licata, where their tiny house caught the fragrant sea breezes from the Mediterranean. They lived in one of the true garden spots of the earth, but their Eden was ruined by poverty and violent criminals. This is exactly why Tommaso chose to bring Josephine and the children to America, where the opportunity is endless, poverty can be reversed, and laws protect the citizens.

As it still is to most immigrants, America is an immense challenge to Josephine. At first, she probably wakes up in the morning and wonders why she has traded the poverty of Sicily for the poverty of America. She misses the Sicilian coast more than she can express. On many hot Brooklyn nights, longing for her home while Tommaso works a brutal late second shift on the docks as a loader, she must feel claustrophobic. At night in Licata, the ocean sends cool breezes into town; on those gentle winds are fragrant hints of African orange blossoms and Greek olive trees. Licata smells of wild orchids and other subtropical coastal blossoms, of scupazzu, the dwarf palms that grow everywhere, sweating in the hot sun. It is an identifiable combination carried subtly on the breezes of the Sicilian coast, that made Josephine feel heady as if from wine.

She whispers of these things to Vincent, high up on the asphalt roof above the streets of Brooklyn. She re-creates a romantic, perfect Sicily for him. She speaks to him in Sicilian, which contains threads of Arabic and Spanish, even though it sounds close to Italian, which is actually a dialect of Tuscan. Sicilian has no future tense and, like Sicily itself, no future for Josephine and her family. America is all about the future.

Yet Josephine relates to her son that the sands of the Sicilian coast are the richest witnesses in the world, having seen the arrival of the Greeks, Phoenicians, Romans, Vandals, Carthaginians, Saracens, Normans, Germans, and Spaniards. He is fascinated by the history of Sicily, by the thousands of years of cultural invasions, and thus the true complexity of being Sicilianu. Like all good mothers, each night Josephine must exhaust her already tired body and mind trying to get Vincent calmed down by telling him stories.

Josephine insists on calling Vincent "Jimmy" (in her strong accent it comes out "Jeemie"), for which he rebukes her. He is Vincent Gibaldi, and he doesn't like the name James. Even though it is a solid American name, he refuses to let anyone call him anything but Vincent. He makes fun of his mother's thick accent when she tries to say "Jimmy." She is the only person who will ever call him this.

The children in the Brooklyn schools are unusually tough and often violent. They have inherited a legacy of brutal behavior from the unfortunate traditions of the Five Points area, mirroring the adults in their lives. Even in the youngest grades, the public schools are alarming examples of survival of the fittest. It becomes the sad duty of all immigrant parents to go about converting their sweet children into survivors.

Josephine tells Vincent old Sicilian stories about strong-willed youngsters who were forced into violent, adult actions in order to avenge the wrongs done to their loved ones. These are the Sicilian versions of Robin Hood and the romanticized American West, imbued with a liminal coming-of-age mystique. They will hopefully better prepare Vincent for the streets of Brooklyn.

The folk tales are epic, about the outlaw heroes of Sicily, mythologies that have been expanded from generation to generation and grow with each telling. They recount adventures of violence, robbery, and revenge that have acquired a patina of Sicilian mores over many hundreds of years, imparting the wisdom of the peculiar codes of conduct, justice, and honor. For Josephine, they define much of what she's been taught about men, although she knows that her own husband toils more fearsomely in America than the protagonists of her stories. She wants to make sure, however, that Vincent understands the responsibilities of manhood from her Sicilian perspective. She relies on the entertainment value of her son's imagination.

Vincent loves every sport; he is always moving, always running. Getting him to sleep is still a never-ending struggle. He denies he is tired until he literally drops, which makes Josephine feel close to dropping as well. She combines her lessons of manliness with the only method she knows to get him to bed: he can be counted on to beg for a story. Josephine will always give in, because it is still their tradition and she feels relieved to have him remain still.

She recounts to Vincent tales of vinnitta. He will be restless with feelings of pride as he hears about resourceful Sicilians carrying out their revenge. Vincent must feel the hot rush of blood to his face, little needle pricks of emotion, spawned by the overwhelming, self-righteous sense of justice. These cathartic rhythms simmer inside him. He is already tightly in control of his emotions, having learned this from the rare hours spent with his father. Life is demanding, and men are serious. From these stories, Josephine is able to instruct him, hopefully giving him a better ability to see what is coming in the schoolyard and on the streets before he becomes a casualty.

She wants their share of the promises of America, but education for the poor comes with a high price. She expands her storytelling to include all of the cautions that reflect her gravest worries for her greenhorn children out on the mean streets. The immigrant experience, especially in New York, is initially a dialogue of survival.


Excerpted from Deadly Valentines by Jeffrey Gusfield. Copyright © 2012 Jeffrey Gusfield. Excerpted by permission of Chicago Review Press Incorporated.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
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Meet the Author

Jeffrey Gusfield, a native Chicagoan, has researched the history of Jack McGurn, Louise Rolfe, and the Capone years for more than four decades.

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Deadly Valentines: The Story of Capone's Henchman "Machine Gun" Jack McGurn and Louise Rolfe, His Blonde Alibi 3 out of 5 based on 0 ratings. 2 reviews.
Anonymous More than 1 year ago
A wonderfully written and thoroughly researched work.
Anonymous More than 1 year ago
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